Molecular recognition directed supramolecular control over perylene-bisimide aggregation resulting in aggregation induced enhanced emission (AIEE) and induced chiral amplification

Bappaditya Roy, Takao Noguchi, Youichi Tsuchiya, Daisuke Yoshihara, Tatsuhiro Yamamoto, Seiji Shinkai

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Recognition directed spontaneous assembly formation has been used to build-up a sensory system with perylene bis-guanidinium (PBG), which presented great response towards chiral guest sensing. Based on structural modification in the chiral guest molecules, PBG can selectively recognize dibenzoyl tartaric acid (DBTA) among the other tartaric acids (TA), resulting in an explicit read-out of molecular information via the generation of characteristic induced circular dichroism spectra for the D- and L-enantiomers. The binding ability depends only on the substituents in the TA and the local guidance plays an important role in structure formation. The bulky substituents in TA can lead to induced chirality in the cofacial perylene stacks by generating an active angle between the successive transition dipoles. The induced helical sense was found to exhibit efficient chiral amplification with a sigmoidal change (i.e. according to a sergeants-and-soldiers effect) in the enantiomeric excess plot. The diversity in physical properties was further examined by the preparative method. Compared to the simple mixing method, the heating-cooling method is able to show aggregation induced fluorescence enhancement, which was used to fabricate highly efficient fluorescent solid in a supramolecular manner from a perylene-based dye.

Original languageEnglish
Pages (from-to)2310-2318
Number of pages9
JournalJournal of Materials Chemistry C
Volume3
Issue number10
DOIs
Publication statusPublished - Mar 14 2015

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Perylene
Molecular recognition
Amplification
Agglomeration
Acids
Guanidine
Enantiomers
Chirality
Dichroism
Coloring Agents
Dyes
Physical properties
Fluorescence
Cooling
Heating
Molecules
tartaric acid
perylene bisimide

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Materials Chemistry

Cite this

Molecular recognition directed supramolecular control over perylene-bisimide aggregation resulting in aggregation induced enhanced emission (AIEE) and induced chiral amplification. / Roy, Bappaditya; Noguchi, Takao; Tsuchiya, Youichi; Yoshihara, Daisuke; Yamamoto, Tatsuhiro; Shinkai, Seiji.

In: Journal of Materials Chemistry C, Vol. 3, No. 10, 14.03.2015, p. 2310-2318.

Research output: Contribution to journalArticle

Roy, Bappaditya ; Noguchi, Takao ; Tsuchiya, Youichi ; Yoshihara, Daisuke ; Yamamoto, Tatsuhiro ; Shinkai, Seiji. / Molecular recognition directed supramolecular control over perylene-bisimide aggregation resulting in aggregation induced enhanced emission (AIEE) and induced chiral amplification. In: Journal of Materials Chemistry C. 2015 ; Vol. 3, No. 10. pp. 2310-2318.
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